2-Phenylethanol → Phenylethyl o-methylcinnamate

HRID 973922Notes

Reaction equation

HRID 973922 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[C:13]1([CH2:19][CH2:20]O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7]

Participants

5

Reactant 2

HCID 60542-PhenylethanolHCID 983063-(2-Methylphenyl)prop-2-enoic acid

Product 1

HCID 53835941Phenylethyl o-methylcinnamateYield 74%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 324.0 g (2.00 moles) of o-methylcinnamic acid, 428.0 g (3.5 moles) of 2-phenylethanol, 10.0 g (0.058 moles) of p-toluenesulfonic acid and 1,200 ml of toluene was refluxed under a water separator. After 15 hours, the calculated amount of water had separated off. The reaction solution was washed first with water and then with saturated sodium bicarbonate solution. The combined washwater was extracted once with ether, and the ether phase was combined with the organic phase. The combined, organic phases were fractionated over a 10 cm Vigreux column. The solvents were separated off under atmospheric pressure and in a vacuum from a water pump. The Vigreux column was replaced by a column head and the product was distilled under 0.01 mm Hg (b.p. 154°-155° C./0.01 mm Hg). 394.0 g of phenylethyl o-methylcinnamate of melting point 52° to 53° C. were obtained.

Workup

  1. customthe calculated amount of water had separated off
  2. washThe reaction solution was washed first with water
  3. extractionThe combined washwater was extracted once with ether
  4. customThe solvents were separated off under atmospheric pressure and in a vacuum from a water pump
  5. distillationthe product was distilled under 0.01 mm Hg (b.p. 154°-155° C./0.01 mm Hg)

Sources & evidence

ORD record
ord-d92555756e58491892b5703d7018e595
Source dataset
uspto-grants-1991_11
Patent number
US05066640

Reaction notes

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